
%0 Journal Article
%A Best, Wayne M. 
%A Ferro, Vito 
%A Harle, Julia 
%A Stick, Robert V. 
%A Tilbrook, D. Matthew G. 
%T The Synthesis of Some Epoxyalkyl <font face = "symbol">b</font>-<emph type="2">C</emph>-Glycosides as Potential Inhibitors of <font face = "symbol">b</font>-Glucan Hydrolases
%J Australian Journal of Chemistry
%D 1997/07/07
%V 50
%N 5
%P 463-472
%K 
%R https://doi.org/10.1071/C97015
%U https://www.publish.csiro.au/paper/C97015 
%X The treatment of tetra-O-benzyl-D-glucono-1,5-lactone with various alkenylmagnesium halides gave the intermediate lactols which, upon reduction (Et3SiH/BF3) and protecting group manipulation, yielded alkenyl tetra-O-acetyl-&#946;-D-C-glucopyranosides in good yield. These &#946;-D-C-glucosides were precursors of the epoxyalkyl &#946;-D-C-glucopyranosides, themselves putative inhibitors of b-glucan hydrolases. Similar additions of Grignard reagents to per-benzylated cellobionolactone were not as successful in yielding epoxyalkyl &#946;-C-cellobiosides. The addition of Grignard reagents to 1,2-anhydro-3,4,6-tri-O-benzyl-&#945;-D- glucose offers a viable alternative route to the prop-2-enyl &#946;-D-C-glucoside, but not to the but-3-enyl and pent-4-enyl counterparts. Likewise, the addition of Grignard reagents to a 1,2-anhydro cellobiose gave disappointing results. Preliminary results are reported for a novel approach to alkenyl &#946;-D-C-glucosides by the alkylation of nitromethyl &#946;-D-C-glucosides. 
